Patent GB-499022-A (GB)
Title: Improvements in the manufacture and production of wetting agents
IPC: D06M13/402
Filed: 1937-04-09
Abstract: Compounds of the general formula <FORM:0499022/IV/1> where Me is hydrogen, and alkali metal, an ammonium radicle or the radicle of an organic base, X is oxygen, sulphur, NH or NY (Y being an organic radicle), R is an aliphatic residue containing at the most 8 carbon atoms, and R1 and R2 are aliphatic radicles containing more than 3 carbon atoms each and together more than 11 carbon atoms, are manufactured by reacting amines NHR1R2 with aliphatic monocarboxylic acids containing at the most 9 connected carbon atoms and containing reactive halogen, hydroxyl groups, nitrogen atoms with at least one attached hydrogen atom, or double linkages, or with a derivative (anhydride, halide or ester) of such acid, and treating the resulting amides with the usual sulphonating agents if hydroxyl groups or double linkages are present, with chlorsulphonic acid, fluorosulphonic acid or sulphur trioxide if nitrogen is present, or with thiosulphates if reactive halogen is present in the acyl radicle (whereby radicles HO3SX-, where X is oxygen, NH or NY, or, when employing thiosulphates, ZO3S2, where Z is the metal contained in the thiosulphate, are introduced), and, if desired, subsequently replacing the hydrogen of the radicles HO3SX- by alkali metals, ammonium radicles or radicles of organic bases.  The amines NHR1R2 may be employed in the form of their salts, in which case it is preferable to work in the presence of acid-binding agents.  The products may be used as assistants in the textile industry, alone or together with other wetting or cleansing agents, and in many cases their wetting power is improved by the presence of constituents of limited water-solubility.  In examples: (1) glycollic acid diisohexylamide, prepared by heating glycollic acid with diisohexylamine, is treated with chlorosulphonic acid in ethereal solution, and the product is neutralized with caustic soda; the amides from glycollic acid or hydroxyethoxyacetic acid with diisoheptylamine or diisooctylamine may be similarly treated; (2) glycollic acid is condensed with a mixture of secondary amines obtained by treating bye-products of the methanol synthesis with alkali, converting the acids formed to nitriles, hydrogenating these in the presence of a nickel catalyst and, if necessary, removing any primary and tertiary amines, and the product is treated as in (1); (3) the mixture of secondary amines obtained by hydrogenating the nitriles of the lower boiling fatty acid from the oxidation of paraffin wax and, if necessary, removing any primary and tertiary amines, are similarly treated.  Other secondary amines specified are those obtainable from alcohols contained in the higher fractions from the catalytic synthesis of isobutyl alcohol, from the alcohols formed by condensation of aldehydes and ketones followed by hydrogenation, from mixtures of isoheptyl and isohexyl alcohols, from isodecylcarboxylic acid and other acids from the oxidation of mineral oil or from the corresponding alcohols.  The Provisional Specification contains a further example according to which chloracet-diisooctylamide is refluxed in methanol solution with sodium thiosulphate. Specifications 341,053, 382,718, and 417,930 are referred to.  Samples have been furnished under Sect. 2 (5) of products prepared as follows: (A) the sulphonation product of (3) is neutralized with ammonia instead of caustic soda; (B) diethylamine is employed for the neutralization; (C) the secondary amine mixture of (3) is heated with the hydrochloride of glycocoll ethyl ester, and the product is stirred with chlorsulphonic acid in ether in the presence of pyridine, and then neutralized with caustic soda; (D) chloracet-diisohexylamide, obtained by reacting chloracetyl chloride with diisohexylamine in the presence of an acid-binding agent, is dissolved in methanol and boiled with an aqueous solution of sodium thiosulphate; (E) a secondary amine mixture of the type described in (3), in which the aliphatic radicles contain 7-9 carbon atoms, is heated with hydroxypivalic acid, and the product is treated with chlorsulphonic acid in ethereal solution and then neutralized with caustic soda.